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Preparation and crystallographic analysis of gliclazide polymorphs.

Rajamma AJ, Sateesha SB, Narode MK, Prashanth VR, Karthik AM - Indian J Pharm Sci (2015 Jan-Feb)

Bottom Line: Polymorph Form-I is found to exist in centro-symmetric triclinic P-1 space group and has endothermic peak at 162.93°.Form-II and Form-III are relatively most stable and least soluble.However, there was no remarkable difference in their aqueous solubility under the conditions in which study was conducted.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, KLEU's College of Pharmacy, Bangalore-560 010, India.

ABSTRACT
Since the introduction of gliclazide in the pharmaceutical industry, a large number of research groups have been engaged in various investigations aiming to enhance its biomedical application. But, very limited efforts have been made to study polymorphism of gliclazide. Therefore, this study focuses on solvent-induced polymorphism of gliclazide and its characterization by thermal methods. Three polymorphs namely, Form-I, II and III and an amorphous powder were produced from different solvents and solvent mixtures. Crystals were analyzed using infrared spectroscopy, differential scanning calorimetry, X-ray powder diffraction and single crystal x-ray diffraction. Polymorph Form-I is found to exist in centro-symmetric triclinic P-1 space group and has endothermic peak at 162.93°. Form-II has endothermic peak from 171.2° to 172.35° and exists in centro-symmetric monoclinic P21/a space group while Form-III has endothermic peak from 168.93° to 169.86° and exists in centro-symmetric monoclinic P21/n space group. The equilibrium solubility values of Form-I, II, III and the amorphous form were 0.4825±0.025, 0.2341±0.042, 0.2581±0.038 and 0.5213±0.072 mg/ml, respectively. The Form-I has relatively higher solubility and similar to that of amorphous gliclazide. Form-II and Form-III are relatively most stable and least soluble. However, there was no remarkable difference in their aqueous solubility under the conditions in which study was conducted.

No MeSH data available.


Molecular structure of gliclazide.
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Figure 1: Molecular structure of gliclazide.

Mentions: Gliclazide, 1-(3-azabicyclo[3.3.0]oct-3-yl)-3-tosylurea; is also noted as 1-(3-azabicyclo[3.3.0]oct-3-p-tolylsulfonylurea (fig. 1). Since its inception in the pharmaceutical industry, a large number of research groups have been intensified in various quests aiming to enhance its biomedical value[91011]. But, very confined efforts have been made to reflect polymorphism of gliclazide. Winters et al., has conveyed solid state characterization of gliclazide polymorphs[12], but their study is confined to powder X-ray diffraction (XRPD), infrared (IR) spectroscopy and differential scanning calorimetry (DSC). Single crystal x-ray diffraction is used to study solid-state properties and crystal structure of gliclazide, but it was limited to characterization of only one polymorph[12]. There upon our studies resort on inspecting the solvent-induced polymorphism of gliclazide[13]. Solvent-induced crystallization technique is applied in this study; as a result the polarity of the recrystallisation solvent and its ability to form hydrogen bonds has a great impact on the polymorphism of gliclazide. The isolated crystal forms were delineated by their melting points, IR spectra, DSC, XRPD patterns, single crystal x-ray diffraction and equilibrium solubility.


Preparation and crystallographic analysis of gliclazide polymorphs.

Rajamma AJ, Sateesha SB, Narode MK, Prashanth VR, Karthik AM - Indian J Pharm Sci (2015 Jan-Feb)

Molecular structure of gliclazide.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4355880&req=5

Figure 1: Molecular structure of gliclazide.
Mentions: Gliclazide, 1-(3-azabicyclo[3.3.0]oct-3-yl)-3-tosylurea; is also noted as 1-(3-azabicyclo[3.3.0]oct-3-p-tolylsulfonylurea (fig. 1). Since its inception in the pharmaceutical industry, a large number of research groups have been intensified in various quests aiming to enhance its biomedical value[91011]. But, very confined efforts have been made to reflect polymorphism of gliclazide. Winters et al., has conveyed solid state characterization of gliclazide polymorphs[12], but their study is confined to powder X-ray diffraction (XRPD), infrared (IR) spectroscopy and differential scanning calorimetry (DSC). Single crystal x-ray diffraction is used to study solid-state properties and crystal structure of gliclazide, but it was limited to characterization of only one polymorph[12]. There upon our studies resort on inspecting the solvent-induced polymorphism of gliclazide[13]. Solvent-induced crystallization technique is applied in this study; as a result the polarity of the recrystallisation solvent and its ability to form hydrogen bonds has a great impact on the polymorphism of gliclazide. The isolated crystal forms were delineated by their melting points, IR spectra, DSC, XRPD patterns, single crystal x-ray diffraction and equilibrium solubility.

Bottom Line: Polymorph Form-I is found to exist in centro-symmetric triclinic P-1 space group and has endothermic peak at 162.93°.Form-II and Form-III are relatively most stable and least soluble.However, there was no remarkable difference in their aqueous solubility under the conditions in which study was conducted.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, KLEU's College of Pharmacy, Bangalore-560 010, India.

ABSTRACT
Since the introduction of gliclazide in the pharmaceutical industry, a large number of research groups have been engaged in various investigations aiming to enhance its biomedical application. But, very limited efforts have been made to study polymorphism of gliclazide. Therefore, this study focuses on solvent-induced polymorphism of gliclazide and its characterization by thermal methods. Three polymorphs namely, Form-I, II and III and an amorphous powder were produced from different solvents and solvent mixtures. Crystals were analyzed using infrared spectroscopy, differential scanning calorimetry, X-ray powder diffraction and single crystal x-ray diffraction. Polymorph Form-I is found to exist in centro-symmetric triclinic P-1 space group and has endothermic peak at 162.93°. Form-II has endothermic peak from 171.2° to 172.35° and exists in centro-symmetric monoclinic P21/a space group while Form-III has endothermic peak from 168.93° to 169.86° and exists in centro-symmetric monoclinic P21/n space group. The equilibrium solubility values of Form-I, II, III and the amorphous form were 0.4825±0.025, 0.2341±0.042, 0.2581±0.038 and 0.5213±0.072 mg/ml, respectively. The Form-I has relatively higher solubility and similar to that of amorphous gliclazide. Form-II and Form-III are relatively most stable and least soluble. However, there was no remarkable difference in their aqueous solubility under the conditions in which study was conducted.

No MeSH data available.